16,18-bis(ethoxycarbonyl)-2,5,8,11,14-pentaoxa-17-thiabicyclo<13.3.0>octadeca-1(18),15-diene | 122372-64-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 16,18-bis(ethoxycarbonyl)-2,5,8,11,14-pentaoxa-17-thiabicyclo<13.3.0>octadeca-1(18),15-diene
• 英文别名: diethyl 2,3,5,6,8,9,11,12-octahydrothieno[3,4-b]-1,4,7,10,13-pentaoxacyclopentadecyn-14,16-dicarboxylate；Diethyl 2,5,8,11,14-pentaoxa-17-thiabicyclo[13.3.0]octadeca-1(18),15-diene-16,18-dicarboxylate
• CAS: 122372-64-9
• 化学式: C₁₈H₂₆O₉S
• 分子量: 418.465
• InChiKey: HLMRBHVKAVCYHC-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67 °C(Solv: methanol (67-56-1))
• 沸点：
  572.4±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  16,18-bis(ethoxycarbonyl)-2,5,8,11,14-pentaoxa-17-thiabicyclo<13.3.0>octadeca-1(18),15-diene 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 60.0~294.0 ℃ 、2.67 kPa 条件下， 反应 5.0h， 生成 2,3,5,6,8,9,11,12-octahydrothieno[3,4-b]-1,4,7,10,13-pentaoxacyclopentadecyne
  参考文献：
  名称：

  含噻吩亚基的冠醚的合成及还原脱硫

  摘要：

  从 2,5-双（乙氧基羰基）-3,4-噻吩二醇和 2,5-二氯-3,4 开始制备含有 3,4-噻吩二基和 3,4-噻吩二基双（亚甲基）亚基作为环成分的冠醚-双（氯甲基）噻吩，分别。含噻吩的冠醚的阮内镍脱硫得到具有两个相邻侧链的冠醚，例如甲基或乙氧基羰基甲基。这些冠醚对碱金属阳离子的萃取能力也通过溶剂萃取法进行了检测。

  DOI：

  10.1246/bcsj.62.838
• 作为产物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 3,4-二羟基噻吩-2,5-二甲酸二乙酯 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 生成 16,18-bis(ethoxycarbonyl)-2,5,8,11,14-pentaoxa-17-thiabicyclo<13.3.0>octadeca-1(18),15-diene
  参考文献：
  名称：

  An extended tetrathiafulvalene redox-ligand incorporating a thiophene spacer

  摘要：

  An extended tetrathiafulvalene derivative incorporating a thiophene spacer and a fused crown-ether unit has been synthesized. This highly delocalized system exhibits remarkable electrochemical recognition Properties for Na+ and Ba2+ as shown by cyclic voltammetry in methylene chloride. This result is attributed to the Proximity between the guest metal cation and the positive charge of the oxidized ligand, which is located on the central conjugated thiophenic part. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.005

文献信息

• Synthesis of large ring 3,4-alkylenedioxythiophenes (ADOT) derivatives via Mitsunobu reaction
  作者：Zhaochao Xu、Joo-Hee Kang、Fang Wang、Seung-Min Paek、Seong-Ju Hwang、Youngmee Kim、Sung-Jin Kim、Jin-Ho Choy、Juyoung Yoon

  DOI：10.1016/j.tetlet.2011.03.062

  日期：2011.6

  4-butylenedioxy)thiophene (BuDOT). In this Letter, we use Mitsunobu reaction to synthesize a series of 3,4-alkylenedioxythiophenes (ADOTs) derivatives with 8- to 16-membered rings. The eight-membered compounds were obtained in high or excellent yield. We also found that the 9- to 16-membered EDOT analogs were obtained in relatively low yield because of the competitive reaction to make dimers. Our method provides an easy

  聚（3,4-乙撑二氧噻吩）（PEDOT）以其优化的电导率，稳定性和高度透明性而著称，这使其成功实现了商业化。PEDOT的这些优异性能主要归因于3位和4位的亚烷基二氧基桥，因此，人们在合成3,4-乙撑二氧噻吩（EDOT）类似物上付出了很多努力。但是，只有很少的同源化合物能够成功合成，例如3,4-丙烯二氧噻吩（PrDOT）或3,4-（1,4-丁烯二氧基）噻吩（BuDOT）。在这封信中，我们使用Mitsunobu反应合成了一系列具有8至16元环的3,4-亚烷基二氧噻吩（ADOT）衍生物。以高收率或优异的收率获得了八元化合物。我们还发现，由于竞争性反应可生成二聚体，因此以相对较低的产率获得了9至16元的EDOT类似物。我们的方法提供了一种简单的方法来修饰乙二氧基噻吩（EDOT），并且这些获得的ADOTs化合物有望成为合成材料化学中使用的功能性π-共轭体系的基础。
• From chains to ladders in co-crystals with 2,3-thiophene-15-crown-5, 2,3-naphtho-15-crown-5, and bis-(18-crown-6)-stilbene constructed by weak hydrogen bonding
  作者：Eduard V. Ganin、Stepan S. Basok、Arkadii A. Yavolovskii、Mark M. Botoshansky、Marina S. Fonari

  DOI：10.1039/c005284c

  日期：——

  For the first time a series of co-crystals of 2,3-thiophene-15-crown-5 1, 2,3-naphtho-15-crown-5 2, bis-(18-crown-6)-stilbene 3 with dithiooxamide a, 1,2,5-oxadiazole-3,4-diamine b, and 3-nitro-1H-1,2,4-triazole c with compositions 1a, 2a, 2b·H22O, 2c, and 3a22 were prepared and their structures were studied by X-ray crystallography. The components in the co-crystals demonstrate the different modes of mutual arrangement and contribution of diverse weak interactions to the final architecture. Infinite chains of the alternating component molecules linked by N–H⋯O hydrogen bonds characterise the structures of 1a and 2a, whereas in the case of 3a22 formation of the loosely packed ladder-type structure was observed. In 2b·H22O the planar naphtho- and oxadiazole moieties demonstrate their edge-to-face arrangement, while in 2c the partially overlapping naphtho- and triazole moieties provide effective face-to-face π–π stacking interactions. The improved synthetic strategy for 1 and 2 is given.

  首次制备了一系列 2,3-噻吩-15-冠醚-5 1、2,3-萘-15-冠醚-5 2、双-(18-冠醚-6)-二苯乙烯 3 与二硫代乙酰胺 a、1,2,5-恶二唑-3,4-二胺 b 和 3-硝基-1H-1,2,4-三唑 c 的共晶体，并通过 X 射线晶体学研究了它们的结构。共晶体中的各组分显示了不同的相互排列模式以及各种弱相互作用对最终结构的贡献。通过 N-H⋯O 氢键连接的交替组分分子无限链是 1a 和 2a 结构的特征，而在 3a22 中则观察到形成了松散的梯形结构。在 2b-H22O 中，平面的萘基和噁二唑分子显示出边缘对边缘的排列，而在 2c 中，部分重叠的萘基和三唑分子提供了有效的面对面 π-π 堆积相互作用。本文给出了 1 和 2 的改进合成策略。
• SONE, TYO;SATO, KAZUAKI;OHBA, YOSHIHIRO, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 838-844
  作者：SONE, TYO、SATO, KAZUAKI、OHBA, YOSHIHIRO

  DOI：——

  日期：——
• Synthesis and Reductive Desulfurization of Crown Ethers Containing Thiophene Subunit
  作者：Tyo Sone、Kazuaki Sato、Yoshihiro Ohba

  DOI：10.1246/bcsj.62.838

  日期：1989.3

  Crown ethers containing 3,4-thiophenediyl and 3,4-thiophenediylbis(methylene) subunits as a ring constituent were prepared starting from 2,5-bis(ethoxycarbonyl)-3,4-thiophenediol and 2,5-dichloro-3,4-bis(chloromethyl)thiophene, respectively. A Raney nickel desulfurization of the thiophene-containing crown ethers afforded crown ethers having two adjacent side chains, such as a methyl or ethoxycarbonylmethyl

  从 2,5-双（乙氧基羰基）-3,4-噻吩二醇和 2,5-二氯-3,4 开始制备含有 3,4-噻吩二基和 3,4-噻吩二基双（亚甲基）亚基作为环成分的冠醚-双（氯甲基）噻吩，分别。含噻吩的冠醚的阮内镍脱硫得到具有两个相邻侧链的冠醚，例如甲基或乙氧基羰基甲基。这些冠醚对碱金属阳离子的萃取能力也通过溶剂萃取法进行了检测。
• An extended tetrathiafulvalene redox-ligand incorporating a thiophene spacer
  作者：Gaëlle Trippé、David Canevet、Franck Le Derf、Pierre Frère、Marc Sallé

  DOI：10.1016/j.tetlet.2008.07.005

  日期：2008.9

  An extended tetrathiafulvalene derivative incorporating a thiophene spacer and a fused crown-ether unit has been synthesized. This highly delocalized system exhibits remarkable electrochemical recognition Properties for Na+ and Ba2+ as shown by cyclic voltammetry in methylene chloride. This result is attributed to the Proximity between the guest metal cation and the positive charge of the oxidized ligand, which is located on the central conjugated thiophenic part. (C) 2008 Elsevier Ltd. All rights reserved.